


Indulge

by justanotherbusyfangirl



Category: Supernatural
Genre: Dry Humping, Escort Castiel, Fluff, Hand Jobs, M/M, Semi-Public Sex
Language: English
Status: Completed
Published: 2018-09-22
Updated: 2018-09-22
Packaged: 2019-09-12 03:38:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,275
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16865416
Author URL: https://archiveofourown.org/users/justanotherbusyfangirl/pseuds/justanotherbusyfangirl
Summary: Sam and Jess have been trying to help Dean find a date for their wedding.  Jess comes up with an idea that she insists Dean will like.





	Indulge

Dean shuffled his weight back and forth nervously, not knowing exactly what to expect from the evening ahead of him.  This was all started as a joke, one where Sam teased Dean for not being able to find a date for his and Jess’s upcoming wedding, but it quickly spiraled out of control.

A series of flopped blind dates later – ones set up by both Jess  _and_  Sam – meant that Sam was back to teasing Dean.

* * *

“It’s not my fault you two can’t pick a good person for me!” Dean said exasperatedly over dinner.  Jess cooked for the two of them once a week, and Dean was stuffed from her delicious veal parmesan.  “It’s like you don’t even know me!”

Sam rolled his eyes, practically moving his entire head with the gesture.  “You can’t blame us, Dean!  It’s not  _our_  fault that you go into every one of these dates with a bad attitude!”  Dean huffed, ready to argue but Sam continued before he could get a word in.  “You can’t tell me you didn’t think Jo was awesome, someone you could talk with about anything, or that Benny wasn’t the perfect person for you to veg out with watching football before you’d get distracted.”  Sam made a face proving that his words had taken his mind somewhere he didn’t want to be.

“Yeah, I liked them all fine, but none of them were someone I’d want to  _be with_ , ya know?” Dean argued, trying to get them to see his point of view.  They couldn’t just force him to like someone as more than a friend, it took time to get Dean to open up to people.

Jess, who’d been putting plates away in the kitchen, stepped into the doorway with a huge grin on her face.  “I’ve just had the most wonderful idea,” she announced.  Sam immediately smiled at her and Dean could practically gag at how adoring his brother was toward his fiancé.  

“What?” Dean asked, almost not wanting to know what was happening in Jess’s mind.  She grinned, eyes sparkling like the mischievous Cheshire Cat that she was.

“Not telling you yet.  But prepare yourself for a date Friday,” she instructed.  “I promise you, this will be unlike anything we’ve put you through so far.  I’ll text you the details Friday evening so you don’t have time to back out.”

Dean was worried now, but he knew better than to argue with Jess.  “Fine,” he grumbled, crossing his arms.  Sam looked victorious, even though he was currently in the dark about Jess’s plan just like Dean was.

* * *

Looking back at that conversation, Dean should have known better.  He looked at the group text on his phone, re-reading the conversation between him, Jess, and Sam.

Jess:  _Okay Dean, your date will be there to pick you up at 7 pm.  Look sharp, wear a suit.  You’re going to get swept off your feet, I just know it!_  
Dean:  _Who’s my date?  You gave a blind date my address to pick me up?_  
Sam:  _Oh, don’t you worry, Dean.  Confidentiality is key with this one._  
Dean:  _What?!?!  What does that even mean?_  
Jess:  _Your date is an escort, Dean.  I paid him to make sure you have a really good time tonight.  Just trust me, he’s going to rock your world._

Sam’s response was a gif of people dancing, party-style.  Dean thought he was going to be sick.

A knock on Dean’s door made him jump, before he mentally reprimanded himself.  It was seven o’clock, on the dot.  He shouldn’t have been scared, but he was about to open the door to an escort – a hooker.  What was Jess thinking?

Before Dean could stop himself, his feet took him to his door and his hand opened it, not even bothering to look through the peephole first.

Once the door was open, he realized that was probably a good thing.  He’d have never opened the door if he had any time to prepare.

“Cas?” Dean said incredulously, wondering what the hell was going on.  His old friend Cas Novak, who he’d known through school growing up and kept in contact with relatively well after graduation, was standing in his doorway.  For a moment Cas looked surprised before a mask fell over his face and he smiled.

“Dean Winchester, how are you?” Cas asked, holding his hand out for Dean to shake.  Dean took it, too confused to do anything else.  

“I’m good, Cas, it’s good to see you,” Dean replied, surprised that he meant the words he was saying.  It really was good to see Cas, especially looking the way he did.  He was wearing a blue tailored suit, one that hugged the muscles in his arms just right and was the perfect amount of snug on his lower half.  

Not that Dean was looking Cas up and down, of course.

Dean suddenly remembered what he was doing and he cleared his throat.  “Look, this sucks man, but I’ve got plans tonight.  I didn’t know you were in town, or I’d have cleared my schedule…”

Cas waved his hand dismissively, smiling broadly.  “Dean, I know you have plans tonight,” he said.  Dean’s stomach turned, wondering what Cas was doing here then.  Cas’s next words froze Dean in place.  “Why else would you think I’m standing in your doorway?”

Dean sputtered.  “You- but… Jess – what?”

Cas laughed, a sound that sent shivers down Dean’s spine.  “I suppose Jess – is that Sam’s Jess? – is the one who booked me for the night and not you?”

Dean’s eyes bugged.  “You’re my, my date?” he stammered.  Cas nodded.  “How did…what?”

Cas laughed again, turning slightly and holding his arm out.  “How about we get out of your doorway and we can talk at dinner.  I have reservations for 7:30 and I’d hate for us to be late.”

Dean couldn’t argue, he only nodded and closed his apartment door, locking it before taking Cas’s arm.  He couldn’t help but admire the muscled strength he felt there, but he had to admit he felt silly being led down his own hallway by Cas, who was a few inches shorter than him and apparently his  _escort date for the evening_.

This was sure to be a night he’d never forget.

The car ride to the restaurant was quiet, just a few mumbled words to check on the music, temperature, and location of the restaurant.  Dean sat awkwardly in the passenger seat, wishing he’d asked Cas to take his Baby instead of Cas’s fancy car.

When they got to the restaurant, though, Dean was glad for Cas’s fancy car.  It fit right in with the other fancy cars in the valet line, and Dean wasn’t sure if he would impress or disgust these people with his classic car.  Sure, he loved her to the moon and back, but some people just didn’t know real beauty.

The valet service opened Dean’s car door for him, so he just met Cas at the door to the restaurant after Cas got the ticket.  They smiled at each other before heading inside, Dean suddenly made aware of the reputation of the restaurant.

The room was very dimly lit, candles and small light fixtures lighting each table individually.  There were a handful of tables in the middle of the room, but only a couple were filled.  Most of the patrons were in booths along the edge of the room – booths that had curtains to close for privacy.  About half of the curtains were currently closed.

What had Dean gotten himself into?  Had Jess chosen this restaurant, or had Cas?

He wasn’t sure which of them he’d rather have chosen it.

The hostess guided them to one side of the room, gesturing them into a booth.  When Dean stepped in, he realized that it was a semi-circle, which meant that he and Cas could slide to sit right next to each other if they wanted to.  For now, Dean stayed on his side, grateful when Cas mirrored his actions.  The curtain, slightly see-through from this side, had just barely closed before a waiter came by, bottle of wine in hand.  

“Sirs?” he asked, holding the wine out.  Cas gestured to his glass, letting the waiter pour a small, tasting amount into it.  Dean watched as Cas swirled, sipped, and tasted the wine, holding it in his mouth a moment before he nodded.  The waiter filled their glasses before dropping the menus off and disappearing, curtain closing behind him.

By the amused look on Cas’s face, Dean figured his eyes were bugging out from surprise.  He couldn’t help it, though, so he just stared at his date.

“Cas, what’s going on?” Dean asked.  There were a million questions running through his mind, but he couldn’t put most of them in words.  Now that he was here, on a date with Cas, his mind was already a little fuzzy.  He picked up his wine glass and took a long sip.

“I have to admit,” Cas started, “I wasn’t expecting to be on a date with you like this, Dean.”  Dean thought to ask what Cas meant by  _like this_ , but he couldn’t get the words out before Cas continued.  “I work for an escort company, one that apparently Jess hired to take you out.  We don’t find out our client names until a few hours before the dates, and still it’s never last names.  I was just as surprised as you were to find that you are my client for the evening.”

Dean could only nod, taking another sip of wine.

“I do know that I was hired to help you loosen up, and would potentially have a second date with you to a wedding,” Cas continued.  “I’m assuming – as long as this Jess is Sam’s Jess – that the wedding is your brother’s?”

Dean nodded.  “Yep, Sammy’s getting hitched.  They’ve been putting me up on dates for weeks now, but nothing has worked out.  The other day Jess said she had an idea, but I never would have thought she’d hire a date for me, let alone that my date would be  _you_.”

Dean was embarrassed, to say the least.  It would be one thing to have a hired date in general, but to have a hired date that was someone he knew?  This was completely different territory.

Cas seemed to understand.  “It’s alright, Dean.  This is a bit strange for me, too.”  He paused, seeming to think carefully about his next words.  “I actually, I’ve broken one of the company policies already tonight.”

Dean leaned forward unconsciously, interested in what Cas had done.

“We aren’t supposed to have clients that we know personally.  When you opened the door,” Cas looked up at Dean to meet his gaze, “I should have excused myself then.  But… it was you.”

Dean didn’t know what Cas meant by that, but his stomach flipped with the way Cas said the words.

“What do you mean, Cas?” he prompted, his voice lowered with interest.

The confident escort persona that Cas had been wearing since just after Dean opened his door earlier seemed to fall away, and Dean recognized the face of his high school friend, a somewhat quiet but brilliant boy that he’d always liked.  Cas fiddled with his napkin.

“I, well…”  Cas smiled to himself.  “I guess I wanted the chance to finally have a date with Dean Winchester, even if it wasn’t completely real.”

There was a moment of quiet between them as Cas’s words sank in.  Did that mean that Cas had always liked Dean?  Even in high school?  Dean thought back to their friendship – hanging out playing video games, studying together, going to football games together.  Hell, they’d shared a limo to prom with their (female) dates. 

Truthfully, Cas was the person Dean spent the most time with in high school, besides Sam.

After letting his thoughts go wild for ten, maybe twenty seconds, something flipped inside of Dean and he sat up straighter, a confidence seeping in that he didn’t have before.  He scooted around the booth a bit, until he could grab Cas’s arm and pull him close as well.  Cas moved, even though he was obviously surprised by Dean’s reaction, until they were sitting hip to hip, legs pressed together from hip to foot.

Dean turned his body slightly toward Cas, resting one arm on the booth behind them.  

“Who says this date doesn’t have to be real?” Dean asked, proud of himself for how smooth the line was.  Cas met his eyes, surprise and happiness shining from baby blues.

“Dean –“

Before Cas could respond, Dean leaned forward and closed the space between them, their lips pressing together in a chaste kiss.  When he realized what he’d done, Dean pulled away.

“I’m sorry, I shouldn’t have just done that –“ Dean said, starting to scoot back from Cas.

Cas’s hand reached across Dean’s body, holding Dean’s waist so that he couldn’t move away.  “Don’t apologize.  Just promise you’ll do it again.”

The smile on Cas’s face spread and Dean’s heart skipped a beat, realizing that Cas wanted whatever this was between them.  Dean leaned forward again, but Cas held a finger up.

“One sec,” Cas said, scooting around the booth and fiddling with the curtain.  Dean had forgotten that they were in a public restaurant, making him incredibly aware of the fact that anyone could have seen their kiss.  Cas came back to Dean and smiled.  “No one will bother us until I change that.”

Dean looked over to the curtain, realizing that Cas had put a gold rope on the edge.  It must be some sort of code, he figured.  He didn’t want to think about how Cas knew what to do, at least not right now.  Right now, he just wanted to kiss Cas again.

Cas must have read his mind, because he leaned in to Dean’s embrace easily.  Their lips met, and this time it wasn’t chaste.  Cas’s mouth opened at the request of Dean’s tongue, beginning a dance as old as time.  Dean moaned into Cas’s mouth, his hands reaching out to grasp any part of Cas he could find.  One landed on Cas’s neck, keeping the brunette close, while the other wrapped around Cas’s waist.  

He never wanted to let Cas go.

The sudden and overwhelming possessiveness seemed to come from nowhere, but at the same time Dean thought it might have always been there.  This was Cas.  This was someone he’d known forever, someone he trusted.

Maybe this is what he was looking for all along.

Before Dean really noticed what was happening, Cas had scooted the table away from the booth where they sat, just enough that it was touching the curtain dividing them from the rest of the restaurant.  With a fluid motion that Dean was impressed with, Cas rotated to straddle Dean where he sat on the booth, pressing their groins together.

Dean looked up at Cas’s face, seeing emotion in the eyes that he hadn’t seen in many – if any – of his most recent relationships.  Cas really wanted this, and Dean realized he did, too.

“Where have you been all my life, Cas?” Dean asked, the cheesy line making Cas smile.  Instead of responding with some equally cheesy words, Cas ground his hips down against Dean’s, letting Dean feel the hardening outline of Cas’s dick.

“Doesn’t matter,” Cas answered before swallowing Dean’s moan, beginning a dirty grind between the two of them.  Dean was panting, the feeling of Cas writhing above him and the knowledge that they were only separated from the outside world by a curtain making him hard as stone.  Cas was kissing him again, so Dean’s hands went to grasp Cas’s hips to guide their rocking motion.

A few minutes went by, the temperature in their booth getting warmer and warmer.  Dean broke the kiss, gasping.  “Cas, if we don’t stop, I’m gonna –“

Cas interrupted him with a kiss, stopping the rocking motion but moving his hands between them.  He fumbled for a minute, but soon had Dean’s cock in his hand.  His thumb found the bead of precome on the tip, using it to slick the way for his hand.

“Cas!” Dean hissed as Cas jacked him, a practiced movement that was sure to have Dean coming in no time.

Cas leaned forward, his hand still working between them.  “Come for me, Dean,” he whispered in Dean’s ear before biting the lobe.  Dean’s body seemed to hear the order and respond immediately, as sticky fluid splashed between them just as Cas finished talking.  Dean’s fingers gripped Cas’s hips tight, surely leaving bruises on the skin.  Dean’s body went limp, exhausted from the strength of his orgasm.

“Cas…” Dean whimpered, unbelieving of what just happened.  Cas kissed him, his lips distracting Dean from the fact that Cas had grabbed one of their cloth napkins and was cleaning them as best he could, tucking Dean back into his pants and zipping them up.

Once Dean was put back together and Cas moved to sit back next to him on the booth, he realized what had happened.  “Cas, what about you-?” Dean asked, motioning toward Cas’s lap.

Cas blushed.  “I’m good, Dean,” he said, not meeting Dean’s eyes.  Dean realized that Cas had come just when Dean had, in his pants and untouched.  That only furthered the fact that this was one of the hottest things Dean had ever been a part of.

Dean leaned in to kiss Cas, gentle this time.  Cas smiled.

“So, ah,” Dean started, looking around.  “What now?”

Cas took a deep breath, balling the napkin up and throwing it on the floor.  He seemed to be thinking hard.  “Now,” he started, reaching for Dean’s hand.  He entwined their fingers together.  “Depends on you, I think.”

Dean started to question what Cas meant, but Cas held up his free hand to stop him from speaking.

“If you are interested in this,” Cas motioned between them, “then I will return Jess’s money to her via the company.”  Dean’s stomach dropped when he remembered that he’d basically just had sex with someone who was being paid to be with him.  “I will call them and resign, find some other employment in the area.”  Cas paused, the seriousness in his face surprising Dean.  Was Cas really going to change his whole life for Dean after one night?  “I will be the boyfriend you always wished you could have, if you want me.”

The word boyfriend took Dean by surprise, especially after all of the flopped dates he’d been on recently.  But truthfully, that’s what Dean wanted.  Someone to look after him, that he would look after as well.  Someone to have by his side, someone to take to Sam’s wedding as more than just a date.

The date they were currently on had just taken a serious turn.

But Dean found himself wanting it more than he could ever put into words.

“I wouldn’t force you to do that, Cas,” Dean started, seeing that Cas looked away, interpreting his words as a rejection.  He quickly continued.  “But I would really like to see where this could go, with us.”

Cas’s eyes snapped back up to Dean’s and a smile spread on his face.  Dean smiled too, leaning forward to kiss Cas again.  “I might need some work on the whole boyfriend thing,” Dean admitted, “but I can’t think of anyone I’d rather try with.”

They didn’t move the gold rope from the curtain for quite a while after that, choosing to indulge in each other instead of a meal until much later in the evening.


End file.
